3-(2-Bromoacetyl)pyridine → 2-Oxo-2-(pyridin-3-yl)ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate

HRID 446789Notes

Reaction equation

HRID 446789 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:14]=1.Br[CH2:24][C:25]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)=[O:26]>C(#N)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][C:20]([O:22][CH2:24][C:25](=[O:26])[C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[O:21])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 1514083-(2-Bromoacetyl)pyridineHCID 145002352-(4-(Quinolin-2-ylmethoxy)phenyl)acetic acid

Product 1

HCID 583680262-Oxo-2-(pyridin-3-yl)ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetateYield 60.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(4-(quinolin-2-ylmethoxy)phenyl)acetic acid (2.0 g, 0.006 mol) in acetonitrile (200 mL) were added TEA (1.74 mL, 0.01 mol), and 2-bromo-1-(pyridin-3-yl)ethanone (3.42 g, 0.017 mol) under an inert atmosphere. The reaction mixture was then stirred at RT for 16 h, concentrated in vacuo and the residue was extracted with EtOAc (2×100 mL). The combined organic layers were washed with water, dried over Na2SO4, filtered, and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 2-oxo-2-(pyridin-3-yl)ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate (1.5 g, 54%) as a solid.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionthe residue was extracted with EtOAc (2×100 mL)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto obtain the crude product
  8. customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-38efba5e81f54883a6a4b0ad9bcdfe6e
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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